The Mighty Singles Dating Challenge

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It’s time to make dating FUN again! Been ‘out of the game’ for a while? Got a bit of a dating phobia? Or maybe you’ve just lost your motivation when it comes to dating? Uh huh. I get it. Dating can become tiring. But, when you’re ready to get back into it, or give it a proper shot, this will be the way forward my friends! See we’ve pulled together an epic singles dating challenge – to grow your confidence, get you going on more dates, and actually broadening your mind when it comes to dating.

See so often we think we know what we want. We have a set type. All these boxes to tick. We can become pretty picky. But dating (effectively) is actually all about learning – learning who we click with, learning what is and isn’t important to us, getting to know different people, finding out more about ourselves.

This singles dating challenge will get you doing all of that and more. So how it works…

The Singles Dating Challenge Guideline

So as part of the singles dating challenge, I’m going to give you 25 tasks. Why so many? Because I don’t want you to get stuck on one and let it stop you! Instead, this is a comprehensive list of fun dating challenges to give a good crack!

What You Need To Do:

This dating challenge is best done with friends. If you have other single friends, do it with them – turning it into a competition. If you don’t, just let your friends know you’re doing it and let them hold you accountable. You’re more likely to do this if you have someone to fill in on all the latest dating gossip, or spur you on when you’re out and about! (This is why the singles dating challenge works a million times better when doing it with others. Send them this link now. Get them on board! 😉)

Once you’ve decided you’re doing it, and who you’re doing it with / who’s going to be rooting for you throughout, you need to set a timeframe. I recommend about 6-8 weeks. This means it’s not going on so long that you start to lose interest, but it’s long enough for you to smash out a lot of these dates, without having to cram them into too short of a timeframe and end up overdating. (Ugh!)

Then, it’s pretty simple. All you have to do is complete as many tasks within the timeframe. Each completed task gives you a point (or you might like to create a points system where the harder tasks give you more points, the easier ones, less, it’s entirely up to you.) One thing that is useful is a ‘judge.’ This role should be allocated to one of your friends and it’s then their job to say whether something counts or not. Also, don’t try to cheat, because you know what they say… If you cheat, you’re only cheating yourself. (Haha!)

If You’re Doing The Dating Challenge as a Competition:

When doing the singles dating challenge with other single friends, it’s a battle between the two of you (or group of you) and the person who scores the most points by the deadline, wins. You can set a prize, or simply go for the incentive of gaining that winning pride!

Make sure you have a group chat where you can discuss the challenge as you go along. It will keep you motivated and make it more fun. TRUST ME – you are going to have so many funny stories to share after this!

If You’re Doing The Dating Challenge by Yourself:

If it’s just you against the dating challenge, no problemo. Simply have different ‘prizes’ for scoring different points by the end. So you could say 5-10 gets you afternoon tea with your friends, 11-15 earns you a spa day and the full 25 wins you a weekend away!

You see? It’s all about the incentives and finding extra ways to push you out of your comfort zone. You’ll also learn and grow along the way, so there’s heaps of value as you work through the list. Want to see what’s included in it now? Alright then…

The Singles Dating Challenge Task List

Please note: these tasks are just here for inspiration. You can tweak them / add in your own to make this singles dating challenge suitable for anyone. This is just a base!

  1. Spring clean your dating apps by un-matching people you aren’t interested in. (This will also allow you to sort through to find the ones you potentially are, and reignite the conversation, making this dating challenge a hell of a lot easier!)
  2. Go on a date with someone who wouldn’t usually be your ‘type.’
  3. Go on a date with an ‘old flame!’ No d*ckheads allowed. (Point disqualified if you rekindle with anyone who’s not good for you!)
  4. Go on a date with someone who’s bald. (Uh huh, you know you can rule those guys out sometimes!)
  5. Go on a date with someone who’s the same height, or shorter than you. (For the same reason as above. This is something you need to let go of… Give the guys a chance!)
  6. Give a chat up line to someone you don’t know, in person. Here’s some ideas if you’re unsure where to start!
  7. Write your number on napkin and give it to a stranger you fancy. Uh huh, you can do it! I actually really like this one. You can disappear into thin air, walking away with a smile as you do it, if you like!
  8. Go on a fun date, like bowling or mini golf.
  9. Go on a sporting date. Like badminton, tennis, or get the guy to teach you how to play normal golf even!
  10. Hold eye contact with someone for at least 5 seconds then give them a little smile. Note: you can’t be the first person to look away.
  11. Do a quiz or games night. You could even make it a question game. Here’s 100 conversation starters to get to know your match better.
  12. Go on a date within 7 days of matching with someone.
  13. Go on a date with someone within 48 hours of matching with someone. It’s all about spontaneity and seizing the moment! Just pick someone you seem to instantly click with, so you know it’s worth your time.
  14. Go on a date with someone older than you.
  15. Go on a date with someone younger than you.
  16. Let a friend do your swiping for you on a dating app – and message everyone who matches with you in the next hour after that.
  17. Organise a date yourself, setting the date and time… instead of waiting for them to ask. We are in the twenty first century after all! It’s time to take control.
  18. Ask a random guy you find attractive, for directions.
  19. Flirt with a bar man. (Or woman. Remember, this challenge is inclusive for everyone. You just tweak these challenges to make it suitable for you.)
  20. Go speed dating or virtual speed dating. Don’t knock it until you’ve tried it!
  21. Go on an active walking / hiking date.
  22. Go on a dinner date, or for a picnic, get busy baking… something foodie related for one of your first dates! You can make this as fun or romantic as you like.
  23. Go on an intellectual date (museum, gallery, talk etc) – preferably with someone ‘dorky’! If you’re dorky too, all the better. Be un-shamefully yourself and show those quirks!
  24. Go on a date with someone who was born in a different country. And ask them about this. Learn. Discuss. Really get to know them!
  25. Message someone you’ve always fancied and ask them if they want to meet up next week.
  26. Get introduced to one of your friend’s single friends and give them a proper chance!
  27. Go on a first date with someone you really fancy…. SOBER! This might sound like a funny one, but if you’re anything like me – the nerves can sometimes get the better of you when dating and you can find yourself relying on alcohol to ease them. This isn’t a great habit, so we want to smash this out the water in our singles dating challenge!
  28. Go on a date with someone who you’ve been speaking to on and off, for months, but have never actually met. OR someone who you used to speak to, but haven’t spoken to or seen for a while… it’s time to reconnect!
  29. Ask five people you’re talking to at least five deep questions – Let’s take your connections to the next level and get to know them better! Click here for some question ideas to get the inspiration flowing.
  30. Go on a blind date or a blind double date. Eek!


You can set specific rules and guidelines amongst your friends for the singles dating challenge. A few things I think are worth mentioning however…

  1. This challenge is aimed at people who are open-minded, looking to find love, but not in a rush. It’s usually for those in the start of their dating journey, or picking it back up after a little break.
  2. You can’t keep going dates with the same person and using that one person to work your way through the list, because the more familiar you are with a person, the easier it becomes. This is about pushing yourself – getting to know different people, becoming more open-minded, growing your confidence through a mix of different experiences. You can date one person more than once, but not just that person – and that person alone – for the whole duration of the challenge!
  3. What happens if you catch feelings for someone? Awesome. But remember, it’s not good to fall for someone too fast, and seeing as it’s still early days, it’s still a good idea to get to know other people. Just make sure you’re open and transparent about that with them. If you do see serious potential with this person and you’ve done a few dates with other people but still keep going back to them, that’s when the situation becomes different and the challenge has worked it’s magic to help you find ‘love’ (potentially!) But don’t stop it too early. Remember, if someone’s right for you, the two of you will always be drawn back together anyway.

The only one real ‘rule’ I want to impose on this singles dating challenge is to HAVE FUN WITH IT! That’s the most important thing. But, see how you get on, and if you do give this a go… I want to hear about it.

Good luck my lovelies! Subscribe below for more fun challenges like these.


Singles Dating Challenge

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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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